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08-SEPTEMBER-2008 09:13:22 - 6 fatty acid Merge arrows It has been suggested that this article or section be merged with fatty acid. Discuss For an explanation of n and numerical nomenclature such as n-6 or 18:2, see Nomenclature of fatty acids. Types of fats in food Unsaturated fat Monounsaturated fat Polyunsaturated fat Trans fat Omega fatty acids: ω-3 ω-6 ω-9 Saturated fat Interesterified fat See also Fatty acid Essential fatty acid Food portal The chemical structure of linoleic acid, a common n-6 fatty acid found in many vegetable oils. The chemical structure of linoleic acid, a common n-6 fatty acid found in many vegetable oils. n-6 fatty acids popularly referred to as ω-6 fatty acids or omega-6 fatty acids are a family of unsaturated fatty acids which have in common a carbon-carbon double bond in the n-6 position; that is, the sixth bond from the end of the fatty acid. The biological effects of the n-6 fatty acids are largely mediated by their conversion to n-6 eicosanoids that bind to diverse receptors found in every tissue of the body. The conversion of tissue arachidonic acid 20:4n-6 to n-6 prostaglandin and n-6 leukotriene hormones provides many targets for pharmaceutical drug development and treatment to diminish excessive n-6 actions in atherosclerosis, asthma, arthritis, vascular disease, thrombosis, immune-inflammatory processes and tumor proliferation. Competitive interactions with the n-3 fatty acids affect the relative storage, mobilization, conversion and action of the n-3 and n-6 eicosanoid precursors. See Essential fatty acid interactions for more information. Contents 1 Key n-6 fatty acids 2 Negative health effects 3 Dietary Linoleic Acid Requirement 4 Dietary sources 5 List of n-6 fatty acids 6 See also 7 References 7.1 Additional sources Key n-6 fatty acids Linoleic acid 18:2, n-6, the shortest-chained n-6 fatty acid, is an essential fatty acid. Arachidonic acid 20:4 is a physiologically significant n-6 fatty acid and is the precursor for prostaglandins and other physiologically active molecules. Negative health effects Some medical research suggests that excessive levels of n-6 fatty acids, relative to n-3 fatty acids, may increase the probability of a number of diseases and depression.123 Modern Western diets typically have ratios of n-6 to n-3 in excess of 10 to 1, some as high as 30 to 1. The optimal ratio is thought to be 4 to 1 or lower.45 Excess n-6 fats interfere with the health benefits of n-3 fats; in part because they compete for the same rate-limiting enzymes. A high proportion of n-6 to n-3 fat in the diet shifts the physiological state in the tissues toward the pathogenesis of many diseases: prothrombotic, proinflammatory and proconstrictive.6 Chronic excessive production of n-6 eicosanoids is associated with heart attacks, thrombotic stroke, arrhythmia, arthritis, osteoporosis, inflammation, mood disorders and cancer.7 Many of the medications used to treat and manage these conditions work by blocking the effects of the potent n-6 fat, arachidonic acid.8 Many steps in formation and action of n-6 hormones from n-6 arachidonic acid proceed more vigorously than the corresponding competitive steps in formation and action of n-3 hormones from n-3 eicosapentaenoic acid. 9 The COX-1 and COX-2 inhibitor medications, used to treat inflammation and pain, work by preventing the COX enzymes from turning arachidonic acid into inflammatory compounds.10 See Cyclooxygenase for more information. The LOX inhibitor medications often used to treat asthma, work by preventing the LOX enzyme from converting arachidonic acid into the leukotrienes.1112 Many of the anti-mania medications used to treat bipolar disorder work by targeting the arachidonic acid cascade in the brain.13 Dietary Linoleic Acid Requirement Adding more controversy to the n-6 fat issue is that the dietary requirement for linoleic acid the key n-6 fatty acid, has been seriously questioned, because of a significant methodology error discovered by University of Toronto scientist, Stephen Cunnane.14 Cunnane discovered that the seminal research used to determine the dietary requirement for linoleic acid was based on feeding animals linoleic acid-deficient diets, which were simultaneously deficient in n-3 fats. The n-3 deficiency was not taken into account. The n-6 oils added back systematically to correct the deficiency also contained trace amounts of n-3 fats. Therefore the researchers were inadvertently correcting the n-3 deficiency as well. Ultimately, it took more oil to correct both deficiencies. According to Cunnane, this error overestimates LA requirements by 5 to 15 times. Dietary sources The evening primrose flower O. biennis produces an oil containing a high content of γ-linolenic acid, a type of n-6 fatty acid. The evening primrose flower O. biennis produces an oil containing a high content of γ-linolenic acid, a type of n-6 fatty acid. Four major food oils palm, soybean, rapeseed and sunflower provide more than 100 million metric tons annually, providing more than 32 million metric tons of n-6 linoleic acid and 4 million metric tons of n-3 alpha-linolenic acid 15 poultry eggs cereals whole-grain breads baked goods nuts most vegetable oils evening primrose oil borage oil blackcurrant seed oil flax/linseed oil hemp oil soybean oil cottonseed oil sunflower seed oil corn oil safflower oil pumpkin seeds acai berry List of n-6 fatty acids Common name Lipid name Chemical name Linoleic acid 18:2 n-6 9,12-octadecadienoic acid Gamma-linolenic acid 18:3 n-6 6,9,12-octadecatrienoic acid Eicosadienoic acid 20:2 n-6 11,14-eicosadienoic acid Dihomo-gamma-linolenic acid 20:3 n-6 8,11,14-eicosatrienoic acid Arachidonic acid 20:4 n-6 5,8,11,14-eicosatetraenoic acid Docosadienoic acid 22:2 n-6 13,16-docosadienoic acid Adrenic acid 22:4 n-6 7,10,13,16-docosatetraenoic acid Docosapentaenoic acid 22:5 n-6 4,7,10,13,16-docosapentaenoic acid Calendic acid 18:3 n-6 8E,10E,12Z-octadecatrienoic acid See also Essential fatty acid interactions Essential nutrients n-3 fatty acid n-9 fatty acid References ^ Lands, William E.M. December 2005. Dietary fat and health: the evidence and the politics of prevention: careful use of dietary fats can improve life and prevent disease. Annals of the New York Academy of Sciences 1055: 179-192. Blackwell. doi:10.1196/annals.1323.028. PMID 16387724. ^ Hibbeln, Joseph R. June 2006. Healthy intakes of n-3 and n-6 fatty acids: estimations considering worldwide diversity. American Journal of Clinical Nutrition 83 6, supplement: 1483S-1493S. American Society for Nutrition. PMID 16841858. ^ Okuyama, Hirohmi; Ichikawa, Yuko; Sun, Yueji; Hamazaki, Tomohito; Lands, William E.M. 2007. ω3 fatty acids effectively prevent coronary heart disease and other late-onset diseases: the excessive linoleic acid syndrome. World Review of Nutritional Dietetics 96 Prevention of Coronary Heart Disease: 83-103. Karger. doi:10.1159/000097809. PMID 17167282. ISBN 3805581793. ^ Daley, C.A.; Abbott, A.; Doyle, P.; Nader, G.; and Larson, S. 2004. A literature review of the value-added nutrients found in grass-fed beef products. California State University, Chico College of Agriculture. Retrieved on 2008-03-23. ^ Simopoulos, Artemis P. October 2002. The importance of the ratio of omega-6/omega-3 essential fatty acids. Biomedicine Pharmacotherapy 56 8: 365-379. PMID 12442909. ^ Simopoulos, Artemis P. September 2003. Importance of the ratio of omega-6/omega-3 essential fatty acids: evolutionary aspects. World Review of Nutrition and Dietetics 92 Omega-6/Omega-3 Essential Fatty Acid Ratio: The Scientific Evidence: 1-174. Karger. doi:10.1159/000073788. PMID 14579680. ISBN 3805576404. ^ Calder, Philip C. June 2006. n-3 polyunsaturated fatty acids, inflammation, and inflammatory diseases. American Journal of Clinical Nutrition 83 6, supplement: 1505S-1519S. American Society for Nutrition. PMID 16841861. ^ Smith, William L. January 2008. Nutritionally essential fatty acids and biologically indispensable cyclooxygenases. Trends in Biochemical Sciences 33 1: 27-37. Elsevier. doi:10.1016/j.tibs.2007.09.013. PMID 18155912. ^ Wada, M. August 3 2007. Enzymes and receptors of prostaglandin pathways with arachidonic acid-derived versus eicosapentaenoic acid-derived substrates and products. Nutritionally essential fatty acids and biologically indispensable cyclooxygenases. J. Biol. Chem. 282 31: 22254-22266. ASBMB. ^ Cleland, Leslie G.; James, Michael J.; Proudman, Susanna M. January 2006. Fish oil: what the prescriber needs to know. Arthritis Research Therapy 8 1: 202. BioMed Central. doi:10.1186/ar1876. PMID 16542466. ^ Mickleborough, Timothy D. June 2005. Dietary omega-3 polyunsaturated fatty acid supplementation and airway hyperresponsiveness in asthma. The Journal of Asthma 42 5: 305-314. Informa Healthcare. doi:10.1081/JAS-200062950. PMID 16036405. ^ Broughton, K. Shane; Johnson, Cody S.; Pace, Bobin K.; Liebman, Michael; Kleppinger, Kent M. April 2005. Reduced asthma symptoms with n-3 fatty acid ingestion are related to 5-series leukotriene production. American Journal of Clinical Nutrition 65 4: 1011-1017. American Society for Nutrition. PMID 9094887. ^ Lee, H.J.; Rao, J.S.; Rapoport, S.I.; Bazinet, R.P. November 2007. Antimanic therapies target brain arachidonic acid signaling: lessons learned about the regulation of brain fatty acid metabolism. Prostaglandins, Leukotrienes and Essential Fatty Acids 77 5: 239-246. Elsevier. doi:10.1016/j.plefa.2007.10.018. PMID 18042366. ^ Cunnane, Stephen C. November 2003. Problems with essential fatty acids: time for a new paradigm?. Progress in Lipid Research 42 6: 544-568. doi:10.1016/S0163-78270300038-9. PMID 14559071. ^ Omega-6 fatty acids. WholeHealthMD. Retrieved on 2008-03-23. Additional sources Tokar, Steve 2005-09-02. Omega-6 fatty acids cause prostate tumor cell growth in culture, Medical News Today, MediLexicon International. Retrieved on 2008-03-23. Brain fatty acid levels linked to depression, News-Medical.Net, AZoNetwork 2005-05-25. Retrieved on 2008-03-23. Tribole, E.F. 2006-03-27. Excess Omega-6 Fats Thwart Health Benefits from Omega-3 Fats. British Medical Journal Rapid Responses to Hooper, et. al., 2006. Retrieved on 2008-03-23. v d e Types of Lipids General Saturated fat | Unsaturated fat | Monounsaturated fat | Polyunsaturated fat Geometry Trans fat | Omega-3 fatty acid | Omega-6 fatty acid | Omega-9 fatty acid Phospholipids Phosphatidylserine | Phosphatidylinositol | Phosphatidyl ethanolamine | Cardiolipin | Dipalmitoylphosphatidylcholine Eicosanoids Arachidonic acid | Prostaglandin | Prostacyclin | Thromboxane | Leukotriene Fatty acids Lauric acid | Palmitic acid | Myristic acid | Stearic acid | Caprylic acid Major families of biochemicals Saccharides | Carbohydrates | Glycosides | | Amino acids | Peptides | Proteins | Glycoproteins | | Lipids | Terpenes | Steroids | Carotenoids Alkaloids | Nucleobases | Nucleic acids | | Enzyme cofactors | Flavonoids | Polyketides | Tetrapyrroles Retrieved from http://en..org/wiki/Omega-6_fatty_acid Categories: All articles to be merged | Fatty acids | Essential nutrientsHidden category: Articles to be merged since December 2007 Views Article Discussion this page History Personal tools Log in / create account Navigation Main page Contents Featured content Current events Random article Search Go Search Interaction Community portal Recent changes Contact Donate to Help Toolbox What links here Related changes Upload file Special pages Printable version Permanent link Cite this page Languages Dansk Deutsch Español Français Italiano Português Svenska This page was last modified on 18 July 2008, at 14:00
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